Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure has good color purity, solubility, and thermal stability. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device showing low driving voltage, excellent current and power efficiencies, and significantly improved lifespan can be provided.

The invention claimed is: 
     
       1. An organic electroluminescent compound represented by the following formula 1: 
       
         
           
           
               
               
           
         
         wherein 
         ring A and ring B, each independently, represent any one of the following formulae 2-1 to 2-3: 
       
       
         
           
           
               
               
           
         
         X and Y, each independently, represent —CR 8 — or —N—; provided that both X and Y are not —CR 8 —, simultaneously; 
         R 1  to R 8 , each independently, represent hydrogen, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; and 
         the heteroaryl of the substituted or unsubstituted 3- to 30-membered heteroaryl contains at least one hetero atom selected from N, O and S. 
       
     
     
       2. The organic electroluminescent compound according to  claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino and the substituted alkylarylamino in R 1  to R 8 , each independently, are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkenyl, a 3- to 7-membered heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a 5- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 5- to 30-membered heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl. 
     
     
       3. The organic electroluminescent compound according to  claim 1 , wherein X and Y, each independently, represent —CR 8 — or —N—; provided that both X and Y are not —CR 8 —, simultaneously;
 ring A and ring B, each independently, represent any one of the following formulae 2-1 to 2-3: 
 
       
         
           
           
               
               
           
         
         R 1  to R 8 , each independently, represent hydrogen, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted 5- to 25-membered heteroaryl, or a substituted or unsubstituted di(C6-C20)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring. 
       
     
     
       4. The organic electroluminescent compound according to  claim 1 , wherein X and Y, each independently, represent —CR 8 — or —N—; provided that both X and Y are not —CR 8 —, simultaneously;
 ring A and ring B, each independently, represent any one of the following formulae 2-1 to 2-3: 
 
       
         
           
           
               
               
           
         
         R 1  to R 7 , each independently, represent hydrogen; a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a 5- to 20-membered heteroaryl or a di(C6-C12)arylamino; or a 5- to 20-membered heteroaryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C12)aryl or a di(C6-C12)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; provided that R 1  to R 7  are not hydrogen, simultaneously; and 
         R 8  represents hydrogen or a (C1-C6)alkyl. 
       
     
     
       5. The organic electroluminescent compound according to  claim 1 , wherein
 R 1  to R 7 , each independently, represent hydrogen, a (C1-C20)alkyl, or any one of the following formulae 3-1 to 3-6; or may be linked to an adjacent substituent(s) to form a benzene ring unsubstituted or substituted with a (C1-C6)alkyl, or a naphthalene ring unsubstituted or substituted with a (C1-C6)alkyl; provided that R 1  to R 7  are not hydrogen, simultaneously; and R 8  represents hydrogen or a (C1-C6)alkyl; 
 
       
         
           
           
               
               
           
         
         wherein, 
         Ar 1  and Ar 2 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; provided that Ar 1  and Ar 2  are not fluorenyl; 
         L a , L b , L c , and L d , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-membered heteroarylene; 
         Z represents —S—, —O—, —NR 11 —, or —CR 12 R 13 —; 
         R 11  to R 13 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 7-membered heterocycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 3- to 30-membered, mono- or polycyclic, alicyclic or aromatic ring; 
         R 31  to R 39 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 3- to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; 
         the heteroaryl(ene) and heterocycloalkyl, each independently, contain at least one hetero atom selected from nitrogen, oxygen, and sulfur; 
         a represents an integer of 1 to 3; 
         b to d and f, each independently, represent an integer of 1 to 4; 
         e, g, and h, each independently, represent an integer of 1 to 5; and 
         where a, b, c, d, e, f, g, or h is integers of 2 or more, each of R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , or R 39  may be the same or different. 
       
     
     
       6. The organic electroluminescent compound according to  claim 5 , wherein at least one of R 1  to R 7  is selected from formulae 3-3 to 3-5, and Z of formula 3-3 represents —NR 11 —. 
     
     
       7. The organic electroluminescent compound according to  claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       8. An organic electroluminescent device comprising the organic electroluminescent compound according to  claim 1 .